139626-38-3Relevant articles and documents
The first total synthesis of (+)-goniothalesacetate and syntheses of (+)-altholactone, (+)-gonioheptolide A, and (-)-goniofupyrone by an asymmetric acetate aldol approach
Ankireddy, Sandeep,Ankireddy, Praveen,Sabitha, Gowravaram
, p. 10487 - 10495 (2015)
The first stereoselective total synthesis of (+)-goniothalesacetate and total synthesis of several bioactive styryl lactones, (+)-altholactone, (+)-gonioheptolide A, and (-)-goniofupyrone have been achieved from an advanced intermediate, which can be derived from l-(+)-DET.
Stereoselective synthesis of (+)-goniodiol, (+)-goniotriol, (-)-goniofupyrone, and (+)-altholactone using a catalytic asymmetric hetero-Diels-Alder/allylboration approach
Favre, Annaick,Carreaux, Francois,Deligny, Michael,Carboni, Bertrand
experimental part, p. 4900 - 4907 (2009/06/06)
The stereoselective total synthesis of several members of the styryllactone family was achieved efficiently from common intermediate 8, prepared by a catalytic asymmetric inverse-electron-demand hetero-Diels-Alder/allylboration sequence. The transformatio
First total synthesis and absolute configuration of the styryl lactone gonioheptolide A
Gupta, Shuchi,Rajagopalan, Murali,Alhamadsheh, Mamoun M.,Tillekeratne, L. M. Viranga,Hudson, Richard A.
, p. 3512 - 3518 (2008/09/20)
Efficient asymmetric syntheses of both naturally occurring and non-naturally occurring enantiomers of gonioheptolide A are reported. The absolute configuration of (+)-gonioheptolide A was established by NOESY, Mosher ester analysis, and comparison with the specific rotation of the isolated (+)-gonioheptolide A. Georg Thieme Verlag Stuttgart.
Semisynthesis of new tetrahydrofuranic alkyl ester and furano-pyrone derivatives as inhibitors of the mitochondrial complex I
Peris, Eva,Cavé, Adrien,Estornell, Ernesto,Zafra-Polo, M.Carmen,Figadère, Bruno,Cortes, Diego,Bermejo, Almudena
, p. 1335 - 1342 (2007/10/03)
Methoxymethylation of altholactone (1) led to the corresponding O-methoxymethyl derivative (3) in addition to the unexpected 6,7-dihydro-7-methoxy analogue (4), and two original tetrahydrofuranic (THF) alkyl esters (5,6). Moreover, when we accomplished a new method for the preparation of the furano-pyrone goniofupyrone (7) through 7-hydroxylation of 1 in acid medium, a minor compound (8) with an identical skeleton to that of compounds 5 and 6 was identified. Careful examination of the published spectral data of the reported styryl-lactones with an heptolide skeleton reveals that those structures possess also a THF alkyl ester skeleton. The revision of those structures was confirmed by chemical correlation. All altholactone derivatives assayed proved to be specific inhibitors of the mitochondrial complex I.
Stereoselective Syntheses of (+)-Goniotriol, (+)-8-Acetylgoniotriol, (+)-Goniodiol, (+)-9-Deoxygoniopypyrone, (+)-Altholactone, and (-)-Goniofupyrone
Mukai, Chisato,Hirai, Syuichi,Hanaoka, Miyoji
, p. 6619 - 6626 (2007/10/03)
The γ-lactone intermediate (-)-7, derived from (+)-tricarbonyl(η6-o-(trimethylsilyl)benzaldehyde)chromium(0) complex, was efficiently converted into the corresponding δ-lactone intermediate (-)-11. This second intermediate has been shown to be a versatile compound for stereoselective syntheses of natural styryllactones possessing a six-membered lactone moiety, isolated from Goniothalamus giganteus, by transforming it into (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniodiol, (+)-9-deoxygoniopypyrone, (+)-altholactone, and (-)-goniofupyrone.
First total synthesis and structural elucidation of (-)-goniofupyrone
Mukai, Chisato,Hirai, Syuichi,Kim, In Jong,Hanaoka, Miyoji
, p. 5389 - 5392 (2007/10/03)
The first total synthesis of (-)-goniofupyrone, isolated from Goniothalamus giganteus, was accomplished in a stereoselective manner from (+)-tricarbonyl(η6-2-trimethylsilylbenzaldehyde)chromium(0) complex. This synthesis unambiguously established the relative and absolute stereochemistry of (-)-goniofupyrone.
